W&OD Mile 41-42.5. Based on research by Eugene Scheel, and by on-site research. The W&OD is represented by the green area on the upper right. Ivandale Street connects with the W&OD at the western edge of town, in the upper left.
Many houses are fine examples of Federal-style (1820's) architecture. It is a very long, narrow town. At one time Hamilton was the second-largest town in Loudoun County. In its heyday, it was a summer resort, featuring a boardwalk on which the guests would promenade. The boardwalk ran from the Harmony Methodist Church to Hughes Street. It crossed to the other side of the main street where the concrete sidewalk crosses today.
A fire destroyed most of downtown Hamilton, so one must use one's imagination. Near Harmony Methodist Church was a racetrack for horses. The town staged summer theatricals in a mill, now torn-down, next to the Baptist Church. A black fraternal organization was active in Hamilton after 1920.
- Maplewood, a summer resort house, c. 1810 - 1820. Longtime residence of Gen. Fuller, Commandant, U.S. Marine Corps.
- Masonic Lodge and Hamilton school, lodge was on second floor, 1873 now undergoing rehab.
- Hamilton Baptist Church, 1889 has French Gothic windows.
- Ivy Hall,1895-1900 three-story brick home, now a bed-and-breakfast.
- Church of the Holy Scripture, 1877
- Catholic Distance University, 120 E. Colonial Way. Formerly Miltonia, a boarding house, c. 1850.
- former Farmers & Merchants Bank, 1910, bars still on windows; French mansard roof.
- Harmony Methodist Church and graveyard 1833, rebuilt 1893.
- Hamilton Station, c. 1880
- Waverly Vila, 1872 high-pitched roof and trim.
- Mt. Zion Church, 1881
- former toll house on Snickersville Gap Turnpike, 19th cent., ceased operation in 1870's.
- small store, c. 1920 formerly Laycock's, now Natural Mercantile Grocery.
- one-room schoolhouse, now a private residence. Clapboard and brick nogging, unusual Federal doorway. Town school in 1870's; a field-school in the 1840's and 1850's. Field schools were private, financed by subscription, and located in the most barren part of a farmer's field.
- Braeburn/Solomon Ruse House,
- Brownsville School
- Claude Lowe House, Conrad Bitzer/C.Y. Hall Farmhouse
- Earl Bell House/Gregg House,
- Jonah Sands/Esther Cowart House,
- Love House (1847)
- Hamilton Milling Company,
- Richard Tavenner House/Harmony Hall
- Katy’s Hollow,
- Laycock/Norton House (1880s)
- Mansfield, Maple Lawn,
- Mount Olive Baptist Church,
- Mount Zion Methodist Church,
- Nichols House (Ballenger Lane),
- Offley/Maplewood/McCann House (1780)
- Sears Roebuck House
- Spring House behind Firehouse
- George and Tabitha Tavenner/Winodee Farm (1763)
- Telephone Building.